Oxygen scavenging molecules, articles containing same, and methods of their use

Patent metadata

Field	Value
Publication number	US-9475630-B2
Application number	US-201313849797-A
Country	US
Kind code	B2
Filing date	Mar 25, 2013
Priority date	May 10, 2007
Publication date	Oct 25, 2016
Grant date	Oct 25, 2016

Abstract

The invention relates to compounds of the structure of formula I and II:

where X is selected from the group consisting of O, S and NH; Y, A and B are independently selected from the group consisting of N and CH; D, E and F are independently selected from the group consisting of CH, N, O and S; the symbol ---- represents a single or a double bond; and R 1 , R 2 and R 3 are independently selected from the group consisting of H, electron withdrawing groups and electron releasing groups. In other embodiments, the compounds are used as oxygen scavengers and in barrier compositions and articles.

First claim

What is claimed is:

1. A composition comprising:
a. a base polymer;
b. at least one compound of Formula I or II

wherein X is selected from the group consisting of O, S and NH;
Y, A and B are independently selected from the group consisting of N and CH;
D, E and F are independently selected from the group consisting of CH, N, O and S;
the symbol ---- when used in conjunction with a bond line represents a single or a double bond; and
R 1 , R 2 and R 3 are independently selected from the group consisting of H, electron withdrawing groups and electron releasing groups and a transition metal; and
c. at least one transition metal in a positive oxidation state, said metal being present in the composition in an amount of 10 to 400 ppm;
wherein said compound is present in an amount of about 0.10 to 10 weight percent of said composition.

2. The composition of claim 1 , wherein said at least one transition metal is cobalt.

3. The composition of claim 2 wherein said at least one transition metal further comprises zinc.

4. The composition of claim 1 wherein said base polymer comprises a polyester polymer.

5. The composition of claim 4 wherein the polyester polymer is polyethylene terephthalate.

6. The composition of claim 1 wherein the compound is present in an amount of about 1 to about 10 weight percent based on the weight of the composition.

7. The composition of claim 1 wherein the compound is present in an amount of about 1 to about 5 weight percent based on the weight of the composition.

8. The composition of claim 1 wherein the compound is present in an amount of about 1 to about 3 weight percent based on the weight of the composition.

9. The composition of claim 1 wherein the concentration of transition metal is 30 to 150 ppm.

10. A wall of a package comprising at least one layer, said layer comprising a composition, said composition comprising:
a. a base polymer;
b. at least one compound of Formula I or II

wherein X is selected from the group consisting of O, S and NH;
Y, A and B are independently selected from the group consisting of N and CH;
D, E and F are independently selected from the group consisting of CH, N, O and S;
the symbol ---- when used in conjunction with a bond line represents a single or a double bond; and
R 1 , R 2 and R 3 are independently selected from the group consisting of H, electron withdrawing groups and electron releasing groups and a transition metal; and
c. at least one transition metal in a positive oxidation state, said metal being present in the composition in an amount of 10 to 400 ppm;
wherein said compound is present in an amount of about 0.10 to 10 weight percent of said composition.

11. The wall of claim 10 wherein said at least one transition metal comprises cobalt.

12. The wall of claim 11 wherein said at least one transition metal further comprises zinc.

13. The wall of claim 10 wherein said base polymer comprises a polyester polymer.

14. The wall of claim 13 wherein the polyester polymer is polyethylene terephthalate.

15. The wall of claim 10 wherein the compound is present in an amount of about 1 to about 10 weight percent based on the weight of the composition.

16. The wall of claim 10 wherein the compound is present in an amount of about 1 to about 5 weight percent based on the weight of the composition.

17. The wall of claim 10 wherein the compound is present in an amount of about 1 to about 3 weight percent based on the weight of the composition.

18. The wall of claim 10 wherein the concentration of transition metal is 30 to 150 ppm.

19. A method for packaging an oxygen sensitive material comprising:
a. preparing a package having a wall comprising at least one layer, at least one of said layers comprising a composition, said composition comprising:
a base polymer;
at least one compound of Formula I or II

wherein X is selected from the group consisting of 0, S and NH;
Y, A and B are independently selected from the group consisting of N and CH;
D, E and F are independently selected from the group consisting of CH, N, O and S;
the symbol ---- when used in conjunction with a bond line represents a single or a double bond; and
R 1 , R 2 and R 3 are independently selected from the group consisting of H, electron withdrawing groups and electron releasing groups and a transition metal; and
at least one transition metal in a positive oxidation state, said metal being present in the composition in an amount of 10 to 400 ppm;
wherein said compound is present in an amount of about 0.10 to 10 weight percent of said composition;
b. introducing said oxygen sensitive material into said package; and
c. closing said package.

20. The method of claim 19 wherein said at least one transition metal comprises cobalt.

21. The method of claim 20 wherein said at least one transition metal further comprises zinc.

22. The method of claim 19 wherein said base polymer comprises a polyester polymer.

23. The method of claim 22 wherein the polyester polymer is polyethylene terephthalate.

24. The method of claim 19 wherein the compound is present in an amount of about 1 to about 10 weight percent based on the weight of the composition.

25. The method of claim 19 wherein the compound is present in an amount of about 1 to about 5 weight percent based on the weight of the composition.

26. The method of claim 19 wherein the compound is present in an amount of about 1 to about 3 weight percent based on the weight of the composition.

27. The method of claim 19 wherein the concentration of transition metal is 30 to 150 ppm.

28. A process for making an article comprising:
a. forming a melt by combining in a melt processing zone:
a base polymer,
at least one compound of Formula I or II

wherein X is selected from the group consisting of O, S and NH;
Y, A and B are independently selected from the group consisting of N and CH;
D, E and F are independently selected from the group consisting of CH, N, O and S;
the symbol ---- when used in conjunction with a bond line represents a single or a double bond; and
R 1 , R 2 and R 3 are independently selected from the group consisting of H, electron withdrawing groups and electron releasing groups and a transition metal;
and at least one transition metal in a positive oxidation state, said metal being present in the composition in an amount of 10 to 400 ppm;
wherein said compound is present in an amount of about 0.10 to 10 weight percent of said composition;
b. forming an article from said melt.

29. The process of claim 28 wherein said at least one transition metal comprises cobalt.

30. The process of claim 29 wherein said at least o

Assignees

• Plastipak Packaging Inc

Inventors

• Deshpande Girish Nilkanth
• Weipert Paul David
• Ensley Michael W

Classifications

• C07D209/46

  with an oxygen atom in position 1 · CPC title

• B65D65/38

  Packaging materials of special type or form · CPC title

• C08K5/3432

  Six-membered rings · CPC title

• C08K2201/012

  Additives improving oxygen scavenging properties · CPC title

• C07D207/00 Primary

  Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom · CPC title